$749,000
Original price: $850,000
4 Beds
2.5 Baths
4,073 sqft (on 1.20 acres)
19 High Street, Middlefield, CT 06455
Est. Mortgage $5,268/mo*
Get Pre-QualifiedHome Highlights
Single-Family Home
Built in 1750
1.2 acre lot
$184/sqft
Garage
Local Information
- Map ViewExplore the area around 19 High Street.
- Schools1 Preschool School3 Elementary Schools1 Middle School1 High School
- Shop & Eat
-- mins to
About this House
Older than America, the historic Chilson Bailey House offers a rare opportunity to own a true circa 1750 center-chimney Colonial while enjoying the comfort of a thoughtfully designed 2008 addition. Offering four bedrooms in total, two bedrooms are located within the original 1750 portion of the home, which is not currently livable and requires renovation. This gives the next owner the opportunity to restore an authentic piece of Connecticut history at their own pace while enjoying comfortable living from day one. Everyday living takes place in the 2,963-square-foot addition, featuring a spacious country kitchen with an oversized island, a soaring great room with a floor-to-ceiling stone fireplace, wide-plank pine floors, a first-floor primary suite, and an expansive second-floor loft ideal for a home office, family room, or creative space. Outside, an impressive barn and detached garage offer exceptional space for car collectors, hobbyists, contractors, woodworking enthusiasts, or anyone needing room for projects, equipment, or recreational vehicles. Significant improvements have already been completed, including the addition, detached garage, septic system, 200-amp electrical service, leased solar, and new windows in the original home. For the buyer who sees possibility where others see a project, this is a chance to live comfortably today while bringing the historic heart of an extraordinary Connecticut property back to life.
Last check for updates: about 6 hours ago
Listing courtesy of Debbie D. Huscher, (860) 918-4580
Real Broker CT, LLC, (860) 918-4580
Source: Smart MLS, MLS#24196454
Also Listed on Smart MLS.
Home Details for 19 High Street
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Interior Details Basement: FullNumber of Rooms: 8Types of Rooms: Master Bedroom, Bedroom, Dining Room, Kitchen, Living Room |
Beds & Baths Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 4073 Square Feet |
Appliances & Utilities Appliances: Oven/Range, Refrigerator, DishwasherDishwasherLaundry: Main LevelRefrigerator |
Heating & Cooling Heating: Hydro Air,OilNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Hydro Air |
Fireplace & Spa Number of Fireplaces: 1Has a Fireplace |
Windows, Doors, Floors & Walls Door: French Doors |
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Exterior Home Features Roof: AsphaltPatio / Porch: PatioOther Structures: Barn(s)Foundation: Concrete PerimeterNo Private Pool |
Parking & Garage Number of Garage Spaces: 12Number of Covered Spaces: 12No CarportHas a GarageNo Attached GarageParking Spaces: 12Parking: Barn,Detached |
Frontage Not on Waterfront |
Water & Sewer Sewer: Septic Tank |
Finished Area Finished Area (above surface): 4073 Square Feet |
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Days on Market: 45 |
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Year Built Year Built: 1750 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Antique |
Building Construction Materials: Wood SidingNot a New ConstructionDoes Not Include Home Warranty |
Property Information Parcel Number: 1000699 |
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Price List Price: $749,000Price Per Sqft: $184 |
Status Change & Dates Possession Timing: Negotiable |
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MLS Status: Active |
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Direction & Address City: Middlefield |
School Information Elementary School: John LymanHigh School: Coginchaug Regional |
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Listing Agent Listing ID: 24196454 |
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Building Area Building Area: 4073 Square Feet |
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Community Features: Golf, Lake, Park, Putting Green |
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No HOA |
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Lot Area: 1.2 Acres |
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BasementMls Number: 24196454Attic: Walk-upAttribution Contact: (860) 918-4580Above Grade Unfinished Area: 4073Activation Date: Fri Aug 14 2026 |
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GolfLakeParkPutting Green |
Around this home
What Locals Say about Middlefield
At least 15 Trulia users voted on each feature.
100 % Say there's holiday spirit
100 % Say car is needed
93 % Say yards are well-kept
90 % Say it's dog friendly
84 % Say parking is easy
83 % Say people would walk alone at night
81 % Say there's wildlife
76 % Say kids play outside
75 % Say it's quiet
63 % Say neighbors are friendly
58 % Say they plan to stay for at least 5 years
50 % Say there are community events
39 % Say it's walkable to restaurants
19 % Say streets are well-lit
12 % Say it's walkable to grocery stores
Sourced by Trulia users. Learn more about our methodology.
Market trends in Middlefield
Last updated August 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
14
5MoM
Home Value
Trulia Estimate
$731KSince last month
Increased$4K (+0.5%)Since last year
Increased$223K (+44%)Since last sale
Increased$593K (+429.5%)Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.
Trulia Estimate
The of this home's value increased by +112% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| September 2026 | $731K |
| August 2026 | $727K |
| July 2026 | $520K |
| June 2026 | $522K |
| May 2026 | $506K |
| April 2026 | $486K |
| March 2026 | $468K |
| February 2026 | $427K |
| January 2026 | $453K |
2025 | |
2024 | |
2023 | |
2022 | |
2021 | |
2020 | |
2019 | |
2018 | |
2017 | |
2016 | |
Comparable sales
These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.34 | Single-Family Home | $465,528 | 04/30/26 | 3 | 2.5 | 2,152 | |
0.55 | Single-Family Home | $785,000 | 06/19/26 | 5 | 4 | 3,911 | |
0.23 | Single-Family Home | $475,000 | 04/27/26 | 3 | 1.5 | 1,554 | |
0.63 | Single-Family Home | $415,000 | 09/30/25 | 4 | 3.5 | 2,776 | |
0.77 | Single-Family Home | $246,000 | 05/27/26 | 3 | 1.5 | 1,642 | |
0.79 | Single-Family Home | $705,000 | 04/24/26 | 4 | 3.5 | 2,806 | |
0.22 | Single-Family Home | $310,000 | 09/18/25 | 2 | 1.5 | 610 | |
1.00 | Single-Family Home | $500,000 | 06/12/26 | 3 | 3 | 1,838 | |
0.22 | Single-Family Home | $291,500 | 05/01/26 | 2 | 1 | 756 |
Nearby home prices
Get a sense of expected prices in the area by checking the value of nearby homes.Address | Distance | Price | Bed | Bath | Sqft | Status |
|---|---|---|---|---|---|---|
0.06 | - | - | - | 272 | Off Market | |
0.08 | $530,500 | 3 | 2.5 | 2,063 | Off Market | |
0.08 | $646,800 | 4 | 2.5 | 2,614 | Off Market | |
0.09 | $403,700 | 3 | 2 | 2,576 | Off Market | |
0.16 | $367,400 | 2 | 1 | 1,080 | Off Market | |
0.22 | $402,300 | 2 | 1.5 | 610 | Off Market | |
0.22 | $291,500 | 2 | 1 | 756 | Recently Sold | |
0.22 | $325,700 | 2 | 1 | 869 | Off Market | |
0.22 | $699,900 | 4 | 4 | 1,871 | For Sale | |
0.23 | $475,000 | 3 | 1.5 | 1,554 | Recently Sold | |
0.24 | $338,600 | 2 | 1 | 850 | Off Market |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Aug 19, 2026 Source: Smart MLS #24196454 | PriceChange | $749,000 Price decreased by 12% |
Aug 14, 2026 Source: Smart MLS #24196454 | Listed For Sale | $850,000 |
Dec 28, 2004 Source: N/A | Sold | $138,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | $9,900 | $332,200 |
Home facts updated by county records
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Debbie D. Huscher, Real Broker CT, LLC, (860) 918-4580
Agent Phone: (860) 918-4580
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
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Frequently asked questions about 19 High Street
- What is the estimated monthly payment for 19 High Street?Based on a $749,000 list price with 20% down at today's rates, the estimated monthly payment for 19 High Street in Middlefield, CT is approximately $5,327 (about $4,066 principal & interest, $1,186 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
- What do residents say about Middlefield?Residents describe Middlefield, CT as well-kept, dog-friendly, and easy to park in. Most residents say you need a car. See homes for sale in Middlefield, CT.
- What are the closest schools to 19 High Street?The closest schools to 19 High Street in Middlefield, CT are Coginchaug Regional High School (rated 7/10), Frank Ward Strong School (Middle, rated 5/10), Frederick Brewster School (Pre-K/Elementary).
- What is 19 High Street estimated to be worth?Trulia's estimated value for 19 High Street in Middlefield, CT is $730,700.
- Does 19 High Street have laundry facilities?Yes, 19 High Street in Middlefield, CT has laundry facilities.
- How big is the lot at 19 High Street?The lot at 19 High Street in Middlefield, CT is about 1.2 acres.
19 High Street, Middlefield, CT 06455 is a 4 bedroom, 3 bathroom, 4,073 sqft single-family home built in 1750. This property is currently available for sale and was listed by Smart MLS on Aug 3, 2026. The MLS # for this home is MLS# 24196454.